Carbocyclic-3'-deoxythymidine

Base Information

• Chemical Name: Carbocyclic-3'-deoxythymidine
• CAS No.: 117957-63-8
• Molecular Formula: C₁₁H₁₆N₂O₃
• Molecular Weight: 224.26
• DSSTox Substance ID: DTXSID30151973
• Nikkaji Number: J302.490C
• Wikidata: Q83018523
• ChEMBL ID: CHEMBL286511
• Mol file: 117957-63-8.mol

Synonyms:C-ddT;Carbocyclic-3'-deoxythymidine;NSC 615823;117957-63-8;NSC615823;2,4(1H,3H)-Pyrimidinedione, 1-(3-(hydroxymethyl)cyclopentyl)-5-methyl-, (1S-cis)-;1-[(1S,3R)-3-(hydroxymethyl)cyclopentyl]-5-methyl-pyrimidine-2,4-dione;2,4(1H,3H)-Pyrimidinedione, 1-[3-(hydroxymethyl)cyclopentyl]-5-methyl-, (1S-cis)-;CHEMBL286511;4'-O-Carba-3'-deoxythymidine;DTXSID30151973;1-[2',3'-Dideoxy-3'-C-(hydroxymethyl)-.alpha.-D-erythropentofuranosyl]-thymine

Chemical Property of Carbocyclic-3'-deoxythymidine

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: 1.254g/cm³
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 224.11609238
• Heavy Atom Count: 16
• Complexity: 351

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CN(C(=O)NC1=O)C2CCC(C2)CO
• Isomeric SMILES: CC1=CN(C(=O)NC1=O)[C@H]2CC[C@H](C2)CO

Technology Process of Carbocyclic-3'-deoxythymidine

There total 31 articles about Carbocyclic-3'-deoxythymidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

5-Methyl-1-((1S,3R)-3-trityloxymethyl-cyclopentyl)-1H-pyrimidine-2,4-dione (883742-51-6) → (-)-carba-2',3'-dideoxythymidine (117957-63-8)

Guidance literature:

With trifluoroacetic acid; In methanol; dichloromethane; at 20 ℃; for 10h;

DOI:10.1002/ejoc.200500719

Reference yield: 85.0%

(+/-)-N-<aminocarbonyl>-3-methoxy-2-methyl-2-propenamide (78795-19-4) → (+/-)-1--5-methyl-2,4(1H,3H)-pyrimidinedione (78795-25-2,117957-63-8)

Guidance literature:

With sulfuric acid; for 3.5h; Heating;

Reference yield:

((1R,3S)-3-Azido-cyclopentyl)-methanol (117901-52-7) → (-)-carba-2',3'-dideoxythymidine (117957-63-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / H₂ / 10percent Pd-C / methanol

2: 2.) 25percent NH₄OH / 1.) Et₂O, DMF, PhH, -15 deg C, 3 h; 2.) water, reflux, 3 h

With ammonium hydroxide; hydrogen; palladium on activated charcoal; In methanol;

DOI:10.1016/0040-4039(88)85259-6

upstream raw materials:

(E)-3-methoxy-2-methylacryloyl isocyanate

(1S,3R)-1-amino-3-(hydroxymethyl)cyclopentanone

5-Methyl-1-((1S,3R)-3-trityloxymethyl-cyclopentyl)-1H-pyrimidine-2,4-dione

6'-carba-2'-deoxy-3'-O-phenoxythiocarbonyl-5'-O-tritylthymidine

Downstream raw materials:

Benzoic acid (1S,3R)-3-(4-chloro-5-methyl-2-oxo-2H-pyrimidin-1-yl)-cyclopentylmethyl ester

(+/-)-1--5-methyl-2,4(1H,3H)-pyrimidinedione benzoate

Refernces

• 1、 Ludek, Olaf R.,Balzarini, Jan,Meier, Chris. "Synthesis and antiviral evaluation of carbocyclic 3′-azidothymidine (AZT) analogues and their cycloSal-phosphate triesters". . p. 932 - 940. Retrieved 2007/10/03.
• 2、 Baumgartner,Bodenteich,Griengl. "Chemo-enzymatic synthesis of (-)-carba-2',3'-dideoxythymidine and (-)-carba-2',3'-dideoxy-3'-fluorothymidine". . p. 5745 - 5746. Retrieved 2007/10/02.